Antibacterial macrocycles with substituted biphenyl
a technology of antibacterial macrocycles and biphenyl, which is applied in the direction of biocide, antibacterial agents, drug compositions, etc., can solve the problems that natural products do not meet the requirements in terms of their properties, and achieve the effect of improving the spontaneous resistance rate against s
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example 1b
(5-Bromo-2-chlorophenyl)methanol
[0317]
[0318]10 g (42.5 mmol) of 5-bromo-3-chlorobenzoic acid are dissolved in 135 ml of THF. At 0° C., 4.2 g (55.2 mmol, 5.24 ml) of borane-dimethyl sulfide complex are added dropwise. The mixture is then stirred at RT for 25 min and under reflux for 30 min. 40 ml of water and 15 ml of 2N hydrochloric acid are successively added dropwise while cooling in ice, followed by stirring at RT for 45 min. After a renewed addition of 15 ml of 2N hydrochloric acid the mixture is extracted several times with diethyl ether. The combined organic phase is washed successively with 1N hydrochloric acid, water, a saturated sodium bicarbonate solution and a saturated sodium chloride solution, dried over magnesium sulfate and concentrated in vacuo. The solid is dried under high vacuum to constant weight.
[0319]Yield: 9.1 g (97% of theory) HPLC (method 11): Rt=4.22 min MS (EI): m / z=220 (M)+1H-NMR (300 MHz, CDCl3): δ=1.90 (t, 1H), 4.75 (d, 2H), 7.20 (d, 1H), 7.35 (dd, 1H),...
example 2b
5-Bromo-2-chlorobenzaldehyde
[0320]
[0321]18 ml (0.26 mol) of DMSO are introduced into 64 ml of dichloromethane and, at −78° C., 16.1 g (0.127 mol, 11.1 ml) of oxalyl chloride are added. After 30 min, a solution of 13.1 g (59 mmol) of (5-bromo-2-chlorophenyl)methanol in 100 ml of chloroform is added dropwise. After 20 min, 40 ml of triethylamine are added and the reaction mixture is slowly warmed to RT. After the addition of 50 ml of water the mixture is extracted several times with ethyl acetate. The combined organic phases are washed successively with 2N hydrochloric acid, water, a saturated sodium bicarbonate solution and a saturated sodium chloride solution. The organic phase is dried over magnesium sulfate and concentrated in vacuo. The resulting solid is dried Yunder high vacuum to constant weight.
[0322]Yield: 12.7 g (94% of theory) HPLC (method 11): Rt=4.65 min MS (EI): m / z=218 (M)+1H-NMR (300 MHz, CDCl3): δ=7.32 (d, 1H), 7.65 (dd, 1H), 8.03 (d, 1H), 10.4 (s, 1H).
example 3h
2-(Benzyloxy)-3-fluorobenzaldehyde
[0323]
[0324]9.0 g (64 mmol) of 3-fluoro-2-hydroxybenzaldehyde are dissolved in 200 ml of DMF, 10.7 g (77.1 mmol) of potassium carbonate and 8.4 ml (12 g, 71 mmol) of benzyl bromide are added and the mixture stirred at 80° C. for 24 h. The mixture is poured into 600 ml of water, extracted several times with ethyl acetate, and the organic phase is dried over sodium sulfate, concentrated in vacuo and dried under high vacuum. The crude product is purified by silica gel chromatography (cyclohexane:ethyl acetate 2:1).
[0325]Yield: 14.3 g (97% of theory) HPLC (method 11): Rt=4.82 min. MS (DCI): m / z=231 (M+H)+1H-NMR (300 MHz, CDCl3): δ=5.26 (s, 2H), 7.10 (mc, 1H), 7.31-7.43 (m, 6H), 7.58 (dd, 1H), 10.25 (s, 1H).
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